20696-64-4

Basic information

• Product Name: Z-TRP-NH2
• Synonyms: Z-L-TRYPTOPHAN AMIDE;Z-TRYPTOPHAN-NH2;Z-TRP-NH2;N-ALPHA-CARBOBENZOXY-L-TRYTOPHAN AMIDE;N-[(1S)-2-Amino-1-(1H-indol-3-ylmethyl)-2-oxoethyl]carbamic acid phenylmethyl ester;N-Carbobenzoxy-L-tryptophanamide;N-Cbz-L-tryptophanamide;Z-L-Trp-NH2
• CAS NO: 20696-64-4
• Molecular Formula: C₁₉H₁₉N₃O₃
• Molecular Weight: 337.37
• Mol File: 20696-64-4.mol

Chemical Properties

• Melting Point: 188-189℃
• Appearance: /
• Density: 1.305
• Storage Temp.: Store at RT.
• Solubility: Acetic Acid (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Z-TRP-NH2(CAS DataBase Reference)
• NIST Chemistry Reference: Z-TRP-NH2(20696-64-4)
• EPA Substance Registry System: Z-TRP-NH2(20696-64-4)

Safety Data

• Hazardous Substances Data: 20696-64-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Z-TRP-NH2 is used as an intermediate in the pharmaceutical industry for the synthesis of L-Tryptophanamide Hydrochloride (T89550). Z-TRP-NH2 is important in the development of various pharmaceutical products, particularly those related to the treatment of certain medical conditions.
Used in Research and Development:
In the field of research and development, Z-TRP-NH2 is utilized as a key component in the synthesis of various tryptophan-based compounds. Its role in the creation of these compounds aids in the advancement of scientific understanding and the development of new therapeutic agents.
Used in Chemical Synthesis:
Z-TRP-NH2 is also used as a building block in the chemical synthesis of various tryptophan-containing compounds. Its unique structure allows for the creation of a wide range of molecules with potential applications in different industries, including pharmaceuticals, agrochemicals, and materials science.

Upstream product

• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 133641-28-8 Z-Trp-O-COO-isoBu 
• 50305-28-7 Cbz-L-Tryptophan-OSu 

Downstream Products

• 20696-57-5 L-tryptophanamide 
• 5022-65-1 L-tryptophanamide hydrochloride 
• 1219039-97-0 Nα-[3-(2-fluorophenyl)acryloyl]-L-tryptophanamide 
• 1596353-92-2 (S)-tert-butyl 2-((S)-2-(benzyloxy)carbonylamino-3-(1H-indol-3-yl)propionylamino)hex-3-enoate 

Relevant articles and documents

The Synthesis of Cystine Peptides by Iodine Oxidation of S-Trityl-cysteine and S-Acetamidomethyl-cysteine Peptides

Previously repoted studies of the iodine oxidation of S-trityl-cysteine peptides and S-acetamidomethyl-cysteine peptides, leading directly to cystine peptides, have been extended.Detailed investigations have been made of the reactivities of the S-trityl a

Amidation of carboxylic acids via the mixed carbonic carboxylic anhydrides and its application to synthesis of antidepressant (1S,2R)-tranylcypromine

Primary amidations of carboxylic acids 1 or 3 with NH4Cl in the presence of ClCO2Et and Et3N were developed to afford the corresponding primary amides in 22% to quantitative yields. Additionally, we have applied the amidation to the preparation of various amides containing hydroxamic acids and achieved the synthesis of (1S,2R)-tranylcypromine as an antidepressant medicine via Lossen rearrangement.

AMINO ACID DERIVATIVE

The amino acid derivative of the present invention provides a novel compound that shows excellent analgesic action. The amino acid derivative of the present invention is a novel compound that shows excellent analgesic action to not only a model animal for nociceptive pains but also a model animal for neuropathic pains, so that the amino acid derivative is very useful as a drug for treating various pain diseases.

PROCESS FOR PREPARING VAPREOTIDE

A solution phase process for preparing vapreotide, having the formula:

New active series of growth hormone secretagogues

New growth hormone secretagogue (GHS) analogues were synthesized and evaluated for growth hormone releasing activity. This series derived from EP-51389 is based on a gem-diamino structure. Compounds that exhibited higher in vivo GH-releasing potency than hexarelin in rat (subcutaneous administration) were then tested per os in beagle dogs and for their binding affinity to human pituitary GHS receptors and to hGHS-R 1a. Compound 7 (JMV 1843, H-Aib-(D)-Trp-(D)-gTrp-formyl) showed high potency in these tests and was selected for clinical studies.

Convenient Synthesis of N-Protected Amino Acid Amides

Boc- or Z-amino acids were conveniently amidated at room temperature by a one-pot procedure employing ammonium hydrogencarbonate and N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline in yields of 81-96percent.The benzyl ester-type protector for the side chains of aspartic acid and glutamic acid was not affected by the procedure.

Dichlorotris(dimethylamino)phosphorane as a Dehydratisation Reagent for the Preparation of N-Protected Amino Acid Amides

Besides for the synthesis of peptides and activated esters dichlorotris(dimethylamino)phosphorane (2) now proved to be an excellent reagent for the preparation of N-protected amino acid amides.